Water → 2-Isobutoxy-4-chlorobenzothiazole

HRID 847801Notes

Reaction equation

HRID 847801 reaction equation
Br[C:2]1[S:3][C:4]2[CH:10]=[CH:9][CH:8]=[C:7]([Cl:11])[C:5]=2[N:6]=1.ClC1SC2C=CC=C(Cl)C=2N=1.[OH-].[Na+].O.[CH2:26]([OH:30])[CH:27]([CH3:29])[CH3:28]>>[CH2:26]([O:30][C:2]1[S:3][C:4]2[CH:10]=[CH:9][CH:8]=[C:7]([Cl:11])[C:5]=2[N:6]=1)[CH:27]([CH3:29])[CH3:28]

Participants

6

Reactant 5

HCID 962WaterHCID 6560IsobutanolHCID 14798Sodium HydroxideHCID 771772,4-DichlorobenzothiazoleHCID 771782-Bromo-4-chlorobenzothiazole

Product 1

HCID 127660102-Isobutoxy-4-chlorobenzothiazoleYield 96.8%

Procedure

A mixture (11.30 g, 0.05 mole) of 2-bromo-4-chlorobenzothiazole and 2,4-dichlorobenzothiazole and 94% sodium hydroxide (2.34 g, 0.055 mole) in isobutanol (100 c.c.) was heated under reflux for 1 hour. Water was added and the alcohol was distilled azeotropically together with water. The resulting oily substance was extracted with chloroform, and the chloroform layer was washed with water. The solvent was then removed under reduced pressure to obtain 11.70 g of 2-isobutoxy-4-chlorobenzothiazole as a yellow viscous liquid. Yield 96.8%, purity 97.2%, b.p. 103.5°-105° C./0.15 mmHg.

Workup

  1. temperatureunder reflux for 1 hour
  2. distillationthe alcohol was distilled azeotropically together with water
  3. extractionThe resulting oily substance was extracted with chloroform
  4. washthe chloroform layer was washed with water
  5. customThe solvent was then removed under reduced pressure

Sources & evidence

ORD record
ord-55bbe80eadf74ea0bb1222f57bc645bd
Source dataset
uspto-grants-1981_10
Patent number
US04293702

Reaction notes

Loading…